Water → (2-Chloro-4-nitrophenyl)(6,7,8,9-tetrahydro-5H-pyrido[3,2-b]azepin-5-yl)methanone

HRID 863011Notes

Reaction equation

HRID 863011 reaction equation
[N:1]1[C:11]2[CH2:10][CH2:9][CH2:8][CH2:7][NH:6][C:5]=2[CH:4]=[CH:3][CH:2]=1.C(N(CC)CC)C.[Cl:19][C:20]1[CH:28]=[C:27]([N+:29]([O-:31])=[O:30])[CH:26]=[CH:25][C:21]=1[C:22](Cl)=[O:23].O>ClCCl>[Cl:19][C:20]1[CH:28]=[C:27]([N+:29]([O-:31])=[O:30])[CH:26]=[CH:25][C:21]=1[C:22]([N:6]1[CH2:7][CH2:8][CH2:9][CH2:10][C:11]2[N:1]=[CH:2][CH:3]=[CH:4][C:5]1=2)=[O:23]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 81522Benzoyl chloride, 2-chloro-4-nitro-HCID 124131726,7,8,9-tetrahydro-5H-pyrido[3,2-b]azepine

Product 1

HCID 19699064(2-Chloro-4-nitrophenyl)(6,7,8,9-tetrahydro-5H-pyrido[3,2-b]azepin-5-yl)methanoneYield 67.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a mixture of 2.90 g of 6,7,8,9-tetrahydro-5H-pyrido[3,2-b]azepine, 2.37 g of triethylamine in 40 ml of dichloromethane is added 5.16 g of 2-chloro-4-nitrobenzoyl chloride in 50 ml of dichloromethane. The mixture is stirred at room temperature under argon for 3 hours and then poured into water. The organic layer is separated and washed with 1N NaHCO3, H2O, brine and dried (Na2SO4). The solution is filtered through a thin pad of hydrous magnesium silicate, the pad washed with CH2Cl2 and ethyl acetate and the filtrate concentrated to dryness. The residual solid (7.13 g) is triturated with ethyl acetate to give 4.41 g of off-white crystals, m.p. 143°-145° C.

Workup

  1. customThe organic layer is separated
  2. washwashed with 1N NaHCO3, H2O, brine
  3. dry with materialdried (Na2SO4)
  4. filtrationThe solution is filtered through a thin pad of hydrous magnesium silicate
  5. washthe pad washed with CH2Cl2 and ethyl acetate
  6. concentrationthe filtrate concentrated to dryness
  7. customThe residual solid (7.13 g) is triturated with ethyl acetate

Sources & evidence

ORD record
ord-c6ac7e9c14e847589d2fd70a1e383f73
Source dataset
uspto-grants-1998_02
Patent number
US05719278

Reaction notes

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